Abstract
A convenient synthesis of 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones (DTPs) from 3,3-diamino-2-(arylazo)acrylonitriles through a versatile and readily accessible two-step procedure is described. Density functional theory (DFT) calculations were performed to explain the selectivity of the heterocyclization step, which predominantly afforded 6-amino-5-(arylazo)pyrimidin-2(1H)-thiones in chloroform or ethanol, and 2,3-dihydro-1,2,4-triazines in toluene or DMF. Novel 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones were obtained in good yields and showed absorption in the ultraviolet region and good emission in the blue region. The photophysical properties of DTPs were better than those cited in select literature examples of 8-azapurines. Owing to the facile synthesis and good photophysical characteristics in an aqueous medium, the new DTPs should have potential applications as organic fluorophores in fluorescence imaging and materials science.
| Original language | English |
|---|---|
| Pages (from-to) | 9420-9429 |
| Number of pages | 10 |
| Journal | Organic and Biomolecular Chemistry |
| Volume | 16 |
| Issue number | 48 |
| DOIs | |
| Publication status | Published - 1 Jan 2018 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Biochemistry
- Physical and Theoretical Chemistry
- Organic Chemistry
Cite this
An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core. / Eltyshev, Alexander K.; Suntsova, Polina O.; Karmatskaia, Ksenia D.; Taniya, Olga S.; Slepukhin, Pavel A.; Benassi, Enrico; Belskaya, Nataliya P.
In: Organic and Biomolecular Chemistry, Vol. 16, No. 48, 01.01.2018, p. 9420-9429.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - An effective and facile synthesis of new blue fluorophores on the basis of an 8-azapurine core
AU - Eltyshev, Alexander K.
AU - Suntsova, Polina O.
AU - Karmatskaia, Ksenia D.
AU - Taniya, Olga S.
AU - Slepukhin, Pavel A.
AU - Benassi, Enrico
AU - Belskaya, Nataliya P.
PY - 2018/1/1
Y1 - 2018/1/1
N2 - A convenient synthesis of 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones (DTPs) from 3,3-diamino-2-(arylazo)acrylonitriles through a versatile and readily accessible two-step procedure is described. Density functional theory (DFT) calculations were performed to explain the selectivity of the heterocyclization step, which predominantly afforded 6-amino-5-(arylazo)pyrimidin-2(1H)-thiones in chloroform or ethanol, and 2,3-dihydro-1,2,4-triazines in toluene or DMF. Novel 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones were obtained in good yields and showed absorption in the ultraviolet region and good emission in the blue region. The photophysical properties of DTPs were better than those cited in select literature examples of 8-azapurines. Owing to the facile synthesis and good photophysical characteristics in an aqueous medium, the new DTPs should have potential applications as organic fluorophores in fluorescence imaging and materials science.
AB - A convenient synthesis of 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones (DTPs) from 3,3-diamino-2-(arylazo)acrylonitriles through a versatile and readily accessible two-step procedure is described. Density functional theory (DFT) calculations were performed to explain the selectivity of the heterocyclization step, which predominantly afforded 6-amino-5-(arylazo)pyrimidin-2(1H)-thiones in chloroform or ethanol, and 2,3-dihydro-1,2,4-triazines in toluene or DMF. Novel 2-aryl-2,4-dihydro-5H-[1,2,3]triazolo[4,5-d]pyrimidin-5-ones were obtained in good yields and showed absorption in the ultraviolet region and good emission in the blue region. The photophysical properties of DTPs were better than those cited in select literature examples of 8-azapurines. Owing to the facile synthesis and good photophysical characteristics in an aqueous medium, the new DTPs should have potential applications as organic fluorophores in fluorescence imaging and materials science.
UR - http://www.scopus.com/inward/record.url?scp=85058433471&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85058433471&partnerID=8YFLogxK
U2 - 10.1039/c8ob02644k
DO - 10.1039/c8ob02644k
M3 - Article
C2 - 30500034
AN - SCOPUS:85058433471
VL - 16
SP - 9420
EP - 9429
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 48
ER -